Outreach social work targeting young people has been conducted in Sweden since the 1950s, but its extent has varied significantly depending on the prevailing social policy ideas. Today, we observe a strong expansion, partly motivated by the need to develop preventive strategies against recruitment into gang criminality. The fundamental idea of outreach work is to reach individuals who do not themselves seek the support of social services through contact establishment and motivational work. However, it is not always clear which individuals or in which situations the detached practitioners have the legitimacy to approach the youth they wish to engage. Several factors influence how outreach workers seek out and establish contact with the target group. In this study, participant observations was used to understand what fieldwork entails in practice concerning the outreach and contact-establishing dimensions. It emerges that the location, time, and signals given by the youth themselves indicate how outreach practitioners should seek contact, and with whom. The overarching idea seems to be to establish "good meetings", which means that interactions with the youth proceed smoothly and that a meeting can be an investment that facilitates future contact attempts. This idea results in outreach workers striving to avoid confrontations and to be accepted as adults in an arena where young people are perceived to have significant influence over who is allowed in. The study highlights that the accessibility and receptivity of youth to interactions appear greater when they are in environments with already present adult supervision or control, such as youth centers or sports activities. It seems more challenging